CH647769A5 - Disulfidverbindungen. - Google Patents

Disulfidverbindungen. Download PDF

Info

Publication number: CH647769A5
Authority: CH; Switzerland
Prior art keywords: group; formula; hydroxyphenyl; propanoyl; compound according
Prior art date: 1978-12-30

Application number

CH11528/79A

Other languages

German (de)

English (en)

Inventor

Jun-Ichi Iwao

Masayuki Oya

Tadashi Iso

Original Assignee

Santen Pharmaceutical Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-12-30

Filing date

1979-12-28

Publication date

1985-02-15

1978-12-30 Priority claimed from JP53163964A external-priority patent/JPS6048511B2/ja

1979-01-29 Priority claimed from JP939279A external-priority patent/JPS55102560A/ja

1979-03-17 Priority claimed from JP3133479A external-priority patent/JPS55124757A/ja

1979-06-26 Priority claimed from JP8104379A external-priority patent/JPS565415A/ja

1979-07-03 Priority claimed from JP8482779A external-priority patent/JPS568317A/ja

1979-12-28 Application filed by Santen Pharmaceutical Co Ltd filed Critical Santen Pharmaceutical Co Ltd

1985-02-15 Publication of CH647769A5 publication Critical patent/CH647769A5/de

Links

150000001875 compounds Chemical class 0.000 title claims description 175
-1 acylmercapto Chemical group 0.000 claims description 166
LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 claims description 58
125000000217 alkyl group Chemical group 0.000 claims description 56
125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 48
229950001139 timonacic Drugs 0.000 claims description 42
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
238000000034 method Methods 0.000 claims description 38
125000001424 substituent group Chemical group 0.000 claims description 34
125000003545 alkoxy group Chemical group 0.000 claims description 28
239000000203 mixture Substances 0.000 claims description 25
238000002360 preparation method Methods 0.000 claims description 25
239000002253 acid Substances 0.000 claims description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
125000004432 carbon atom Chemical group C* 0.000 claims description 20
125000004423 acyloxy group Chemical group 0.000 claims description 18
125000003342 alkenyl group Chemical group 0.000 claims description 16
125000003277 amino group Chemical group 0.000 claims description 12
APAUAYLVDHNFBF-UHFFFAOYSA-N 2-(2-hydroxyphenyl)-1,3-thiazolidine-4-carboxylic acid Chemical compound N1C(C(=O)O)CSC1C1=CC=CC=C1O APAUAYLVDHNFBF-UHFFFAOYSA-N 0.000 claims description 11
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
125000005544 phthalimido group Chemical group 0.000 claims description 10
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 10
125000004442 acylamino group Chemical group 0.000 claims description 9
125000003710 aryl alkyl group Chemical group 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
206010012601 diabetes mellitus Diseases 0.000 claims description 7
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
230000008569 process Effects 0.000 claims description 7
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
125000003282 alkyl amino group Chemical group 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 6
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
125000002541 furyl group Chemical group 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
125000005530 alkylenedioxy group Chemical group 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 3
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 3
230000036772 blood pressure Effects 0.000 claims description 3
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
239000007800 oxidant agent Substances 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
MOKXNBYZOABZGQ-SFVWDYPZSA-N (4r)-2-(2-hydroxyphenyl)-3-[3-(propyldisulfanyl)propanoyl]-1,3-thiazolidine-4-carboxylic acid Chemical group CCCSSCCC(=O)N1[C@H](C(O)=O)CSC1C1=CC=CC=C1O MOKXNBYZOABZGQ-SFVWDYPZSA-N 0.000 claims description 2
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000000107 disulfanyl group Chemical group [*]SS[H] 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
150000004678 hydrides Chemical class 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims 4
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
239000008194 pharmaceutical composition Substances 0.000 claims 2
QOHVWAZKSIIFNP-BDAKNGLRSA-N (4r)-3-[(2s)-2-methyl-3-(propyldisulfanyl)propanoyl]-1,3-thiazolidine-4-carboxylic acid Chemical group CCCSSC[C@@H](C)C(=O)N1CSC[C@H]1C(O)=O QOHVWAZKSIIFNP-BDAKNGLRSA-N 0.000 claims 1
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
AZDYQBFYMBALBY-UHFFFAOYSA-N 2-phenyl-1,3-thiazolidin-3-ium-4-carboxylate Chemical compound N1C(C(=O)O)CSC1C1=CC=CC=C1 AZDYQBFYMBALBY-UHFFFAOYSA-N 0.000 claims 1
DKKATFRPTAVOST-LRVUVFPRSA-N 5-(2-hydroxyphenyl)-1-[(2s)-2-methyl-3-(propyldisulfanyl)propanoyl]pyrrolidine-2-carboxylic acid Chemical group CCCSSC[C@@H](C)C(=O)N1C(C(O)=O)CCC1C1=CC=CC=C1O DKKATFRPTAVOST-LRVUVFPRSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 268
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 74
239000000243 solution Substances 0.000 description 68
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 52
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 40
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
239000002904 solvent Substances 0.000 description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
235000011121 sodium hydroxide Nutrition 0.000 description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
239000013078 crystal Substances 0.000 description 17
150000002019 disulfides Chemical class 0.000 description 17
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 16
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
239000003921 oil Substances 0.000 description 15
150000003573 thiols Chemical class 0.000 description 15
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
239000008101 lactose Substances 0.000 description 14
238000010992 reflux Methods 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
229940125904 compound 1 Drugs 0.000 description 12
239000012044 organic layer Substances 0.000 description 12
102000016912 Aldehyde Reductase Human genes 0.000 description 11
108010053754 Aldehyde reductase Proteins 0.000 description 11
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
230000000694 effects Effects 0.000 description 11
239000003513 alkali Substances 0.000 description 10
238000011161 development Methods 0.000 description 10
230000018109 developmental process Effects 0.000 description 10
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
BSHDUMDXSRLRBI-QHGLUPRGSA-N (4r)-2-(2-hydroxyphenyl)-3-(3-sulfanylpropanoyl)-1,3-thiazolidine-4-carboxylic acid Chemical compound SCCC(=O)N1[C@H](C(=O)O)CSC1C1=CC=CC=C1O BSHDUMDXSRLRBI-QHGLUPRGSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
239000003960 organic solvent Substances 0.000 description 9
101800000734 Angiotensin-1 Proteins 0.000 description 8
102400000344 Angiotensin-1 Human genes 0.000 description 8
ORWYRWWVDCYOMK-HBZPZAIKSA-N angiotensin I Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C1=CC=C(O)C=C1 ORWYRWWVDCYOMK-HBZPZAIKSA-N 0.000 description 8
230000005764 inhibitory process Effects 0.000 description 8
239000000843 powder Substances 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
239000007858 starting material Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
150000007513 acids Chemical class 0.000 description 7
239000001913 cellulose Substances 0.000 description 7
229920002678 cellulose Polymers 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
239000005457 ice water Substances 0.000 description 7
239000008279 sol Substances 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
238000005316 response function Methods 0.000 description 6
229910000029 sodium carbonate Inorganic materials 0.000 description 6
235000017550 sodium carbonate Nutrition 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
238000012360 testing method Methods 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
FWNWATHTRVGPDX-RITPCOANSA-N (4r)-3-[(2s)-2-methyl-3-sulfanylpropanoyl]-1,3-thiazolidine-4-carboxylic acid Chemical compound SC[C@@H](C)C(=O)N1CSC[C@H]1C(O)=O FWNWATHTRVGPDX-RITPCOANSA-N 0.000 description 5
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
229920002134 Carboxymethyl cellulose Polymers 0.000 description 5
208000002249 Diabetes Complications Diseases 0.000 description 5
206010020772 Hypertension Diseases 0.000 description 5
229940030600 antihypertensive agent Drugs 0.000 description 5
239000002220 antihypertensive agent Substances 0.000 description 5
239000011575 calcium Substances 0.000 description 5
229910052791 calcium Inorganic materials 0.000 description 5
239000001768 carboxy methyl cellulose Substances 0.000 description 5
235000010948 carboxy methyl cellulose Nutrition 0.000 description 5
239000008112 carboxymethyl-cellulose Substances 0.000 description 5
235000019359 magnesium stearate Nutrition 0.000 description 5
DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical compound OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 description 5
QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 4
206010012655 Diabetic complications Diseases 0.000 description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
239000002585 base Substances 0.000 description 4
238000009472 formulation Methods 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 4
229910052814 silicon oxide Inorganic materials 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
APAUAYLVDHNFBF-JAVCKPHESA-N (4r)-2-(2-hydroxyphenyl)-1,3-thiazolidine-4-carboxylic acid Chemical compound N1[C@H](C(=O)O)CSC1C1=CC=CC=C1O APAUAYLVDHNFBF-JAVCKPHESA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 3
SHBHYINHXNTBRP-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(2-methylsulfonylethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCCS(=O)(=O)C)C=CC=1 SHBHYINHXNTBRP-UHFFFAOYSA-N 0.000 description 3
WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 3
238000009825 accumulation Methods 0.000 description 3
150000008065 acid anhydrides Chemical class 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000002775 capsule Substances 0.000 description 3
229940125782 compound 2 Drugs 0.000 description 3
229940125851 compound 27 Drugs 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
239000003814 drug Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
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239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
235000019645 odor Nutrition 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229960004570 oxprenolol Drugs 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
229960002508 pindolol Drugs 0.000 description 1
PHUTUTUABXHXLW-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=NC=C[C]12 PHUTUTUABXHXLW-UHFFFAOYSA-N 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 description 1
229950010765 pivalate Drugs 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229940113116 polyethylene glycol 1000 Drugs 0.000 description 1
229940057838 polyethylene glycol 4000 Drugs 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
229940020414 potassium triiodide Drugs 0.000 description 1
230000002265 prevention Effects 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
229960003712 propranolol Drugs 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 description 1
OEKUVLQNKPXSOY-UHFFFAOYSA-N quercetin 3-O-beta-D-glucopyranosyl(1->3)-alpha-L-rhamnopyranosyl(1->6)-beta-d-galactopyranoside Natural products OC1C(O)C(C(O)C)OC1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OEKUVLQNKPXSOY-UHFFFAOYSA-N 0.000 description 1
QPHXPNUXTNHJOF-UHFFFAOYSA-N quercetin-7-O-beta-L-rhamnopyranoside Natural products OC1C(O)C(O)C(C)OC1OC1=CC(O)=C2C(=O)C(O)=C(C=3C=C(O)C(O)=CC=3)OC2=C1 QPHXPNUXTNHJOF-UHFFFAOYSA-N 0.000 description 1
OXGUCUVFOIWWQJ-HQBVPOQASA-N quercitrin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OXGUCUVFOIWWQJ-HQBVPOQASA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
206010038464 renal hypertension Diseases 0.000 description 1
238000011160 research Methods 0.000 description 1
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
230000007017 scission Effects 0.000 description 1
LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
239000002002 slurry Substances 0.000 description 1
SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 1
CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
GJNRIGCZVXQSHN-UHFFFAOYSA-M sodium;oxido-oxo-propoxy-sulfanylidene-$l^{6}-sulfane Chemical compound [Na+].CCCOS([O-])(=O)=S GJNRIGCZVXQSHN-UHFFFAOYSA-M 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000013112 stability test Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
238000009495 sugar coating Methods 0.000 description 1
RBTVSNLYYIMMKS-UHFFFAOYSA-N tert-butyl 3-aminoazetidine-1-carboxylate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)N1CC(N)C1 RBTVSNLYYIMMKS-UHFFFAOYSA-N 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
DTMHTVJOHYTUHE-UHFFFAOYSA-N thiocyanogen Chemical compound N#CSSC#N DTMHTVJOHYTUHE-UHFFFAOYSA-N 0.000 description 1
229960004605 timolol Drugs 0.000 description 1
229960004402 tiopronin Drugs 0.000 description 1
231100000820 toxicity test Toxicity 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

CH11528/79A 1978-12-30 1979-12-28 Disulfidverbindungen. CH647769A5 (de)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
JP53163964A JPS6048511B2 (ja)	1978-12-30	1978-12-30	ジスルフイド化合物
JP939279A JPS55102560A (en)	1979-01-29	1979-01-29	Disulfide compound
JP3133479A JPS55124757A (en)	1979-03-17	1979-03-17	Sulfur-containing compound
JP8104379A JPS565415A (en)	1979-06-26	1979-06-26	Ester-type hypotensor
JP8482779A JPS568317A (en)	1979-07-03	1979-07-03	Preventive and remedy for complicating disease of diabetes mellitus

Publications (1)

Publication Number	Publication Date
CH647769A5 true CH647769A5 (de)	1985-02-15

Family

ID=27519061

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH11528/79A CH647769A5 (de)	1978-12-30	1979-12-28	Disulfidverbindungen.

Country Status (10)

Country	Link
US (1)	US4347371A (it)
AU (1)	AU536307B2 (it)
CA (1)	CA1128517A (it)
CH (1)	CH647769A5 (it)
DE (1)	DE2952594A1 (it)
FR (1)	FR2445324A1 (it)
GB (1)	GB2042517B (it)
IT (1)	IT1127323B (it)
NL (1)	NL7909334A (it)
SE (1)	SE446864B (it)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4430344A (en) *	1978-04-08	1984-02-07	Santen Pharmaceutical Co., Ltd.	Antihypertensive 4-thiazolidinecarboxylic acids
JPS5683483A (en) *	1979-12-13	1981-07-08	Santen Pharmaceut Co Ltd	Thiazolidine compound
US4499102A (en) *	1979-12-13	1985-02-12	Santen Pharmaceutical Co., Ltd.	Thiazolidine and pyrrolidine compounds and pharmaceutical compositions containing them
DE3152643A1 (de) *	1980-12-29	1982-12-16	Santen Pharmaceutical Co Ltd	Heterocyclic 5-membered ring compounds
JPS57142962A (en) *	1981-02-28	1982-09-03	Santen Pharmaceut Co Ltd	Cyclodextrin clathrate compound of sulfur-containing compound
US5665770A (en) *	1993-11-05	1997-09-09	Gakko Hojin Kinki Daigaku	Method for treatment of cataract with radical scavenger
DE60227078D1 (de) *	2001-05-30	2008-07-24	Yeda Res & Dev	Allylmercaptocaptoprilverbindungen und deren verwendungen
CA2610922A1 (en) *	2005-06-13	2006-12-21	Yeda Research And Development Co. Ltd.	Use of allylmercaptocaptopril for treating or preventing obesity and obesity related diseases
WO2007086054A2 (en) *	2006-01-25	2007-08-02	Yeda Research And Development Co. Ltd.	A process for preparing allylmercaptocaptopril (cpssa) and related asymmetrical disulfides
CN104945350A (zh) *	2014-03-25	2015-09-30	中国科学院生态环境研究中心	简捷合成高光学纯度噻唑氨基酸的新方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU509899B2 (en) *	1976-02-13	1980-05-29	E.R. Squibb & Sons, Inc.	Proline derivatives and related compounds
AU518147B2 (en) *	1976-12-03	1981-09-17	E.R. Squibb & Sons, Inc.	Derivatives of thiazolidine, thiazine and morpholine carboxylic acids
US4192878A (en) *	1976-12-03	1980-03-11	E. R. Squibb & Sons, Inc.	Derivatives of thiazolidinecarboxylic acids and related acids
JPS5834474B2 (ja) *	1977-06-29	1983-07-27	ウェルファイド株式会社	チアゾリジン誘導体の製造法
ZA783013B (en) *	1978-05-22	1979-06-27	Squibb & Sons Inc	Derivatives of thiazolidinecarboxylic acids and related acids
CA1144930A (en) *	1978-08-11	1983-04-19	Miguel A. Ondetti	Mercaptoacyl derivatives of substituted prolines

1979
- 1979-12-18 US US06/104,970 patent/US4347371A/en not_active Expired - Lifetime
- 1979-12-19 AU AU54024/79A patent/AU536307B2/en not_active Ceased
- 1979-12-20 SE SE7910554A patent/SE446864B/sv not_active IP Right Cessation
- 1979-12-20 CA CA342,420A patent/CA1128517A/en not_active Expired
- 1979-12-28 NL NL7909334A patent/NL7909334A/nl not_active Application Discontinuation
- 1979-12-28 FR FR7932060A patent/FR2445324A1/fr active Granted
- 1979-12-28 IT IT28440/79A patent/IT1127323B/it active
- 1979-12-28 CH CH11528/79A patent/CH647769A5/de not_active IP Right Cessation
- 1979-12-28 GB GB7944544A patent/GB2042517B/en not_active Expired
- 1979-12-28 DE DE19792952594 patent/DE2952594A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
AU536307B2 (en)	1984-05-03
SE446864B (sv)	1986-10-13
GB2042517B (en)	1983-05-25
IT7928440A0 (it)	1979-12-28
FR2445324B1 (it)	1984-03-09
US4347371A (en)	1982-08-31
CA1128517A (en)	1982-07-27
FR2445324A1 (fr)	1980-07-25
AU5402479A (en)	1980-07-03
DE2952594A1 (de)	1980-07-17
GB2042517A (en)	1980-09-24
SE7910554L (sv)	1980-07-01
NL7909334A (nl)	1980-07-02
IT1127323B (it)	1986-05-21

Legal Events

Date	Code	Title	Description
1988-08-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE69122084T2 (de)	1997-04-03	2-arylthiazolderivat sowie dieses enthaltendes arzneimittel
DE69418311T2 (de)	1999-11-04	Isoxazolidindionderivate und deren verwendung
DE2527937A1 (de)	1976-01-08	Benzcycloamidderivate und verfahren zu ihrer herstellung sowie pharmazeutische mittel, worin sie enthalten sind
CH651827A5 (de)	1985-10-15	Carbostyrilderivate, verfahren zu ihrer herstellung und kardiotonische zusammensetzungen, welche diese enthalten.
EP0600949A1 (de)	1994-06-15	Neue 3,5-di-tert.butyl-4-hydroxyphenyl-derivate, verfahren zu ihrer herstellung und arzneimittel.
DE10046029A1 (de)	2002-03-28	Indazole
EP1613600B1 (de)	2015-12-23	Substituierte 4-phenyltetrahydroisochinoline, verfahren zu ihrer herstellung, ihre verwendung als medikament, sowie sie enthaltendes medikament
DD216929A5 (de)	1985-01-02	Verfahren zur herstellung von thiazolidinderivaten
DE4302485A1 (de)	1994-08-04	Piperazinderivate
CH647769A5 (de)	1985-02-15	Disulfidverbindungen.
DE4333761A1 (de)	1995-04-06	Heterocyclische Carbamate, Verfahren zu ihrer Herstellung und Arzneimittel
DE3830060A1 (de)	1990-03-15	2-phenylbenzimidazole - verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel
EP0326106B1 (en)	1994-07-27	Alkylene diamines
DE69203780T2 (de)	1995-12-07	Aminosäurederivate und ihre Verwendung als antiviral Wirkstoffe.
US4483861A (en)	1984-11-20	Antihypertensive sulfur-containing compounds
DE3687283T2 (de)	1993-04-22	Mittel zum schutz des gehirns.
DE69600329T2 (de)	1998-11-05	Benzothiazol-Derivate
DE2801478C2 (it)	1991-01-31
DE3424586A1 (de)	1986-01-09	3-aminocarbonylmethoxy-5-phenyl-pyrazol-verbindungen sowie verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
US4410542A (en)	1983-10-18	Disulfide compounds
CH628622A5 (de)	1982-03-15	Verfahren zur herstellung von neuen in 4-stellung substituierten 3-sulfamoylbenzoesaeuren.
DE4220264A1 (de)	1993-12-23	Phenyl-1,2,5-oxadiazol-carbonamid-2-oxide
EP0362635A1 (de)	1990-04-11	Verfahren von basischen Nitrophenyl-dihydropyridinamiden als Arzneimittel, neue Verbindungen und Verfahren zu ihrer Herstellung über neue Zwischenprodukte
DE2734270C2 (it)	1990-06-21
EP0442348B1 (de)	1996-07-17	Neue Imidazolverbindungen, Verfahren zu deren Herstellung, Arzneimittel auf Basis dieser Verbindungen sowie einige Zwischenprodukte